Tiopronin

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Cat Number

API195322

CAS Number

1953-02-2

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Product Detail Description Customer Q&A

CAS Number

1953-02-2

EINECS

217-778-4

Storage

Store at 2-8°C

Synonyms

N-(2-Mercaptopropionyl)glycine; Thiopronine; Thiola; Tiopronine; 2-(2-sulfanylpropanoylamino)acetic acid; Glycine, N-(2-mercapto-1-oxopropyl)-; Thiolpropionamidoacetic acid

Molecular Formula

C5H9NO3S

Molecular Weight

163.2

Smiles

CC(C(=O)NCC(=O)O)S

Appearance

Whit crystalline solid

Melting Point

93-98°C

Boiling Point

418.3±30.0°C at 760 mmHg (Predicted)

Relative Density

1.3±0.1

General Description

Tiopronin is a synthetic mercaptoacyl derivative with a thiol group, structurally related to cysteine. Its chemical structure is 2-(2-sulfanylpropanamido)acetic acid. Tiopronin is a white to off-white crystalline powder, soluble in water and alcohol. The molecule contains a chiral center, and the drug is available as the racemic mixture.

Mechanism of Action

Tiopronin acts as a reducing agent, breaking the disulfide bonds in cystine and forming a soluble mixed disulfide of tiopronin and cysteine. This reduces the concentration of cystine in the urine, preventing the formation of cystine stones. The drug also has antioxidant properties, scavenging reactive oxygen species (ROS) and protecting cells from oxidative damage.

Application

Tiopronin is indicated for the prevention of cystine kidney stones (cystinuria) in patients who are not responding to conservative measures such as high fluid intake and alkalinization. It is also used for the treatment of rheumatoid arthritis and for the management of heavy metal toxicity. The drug is effective in reducing the frequency of stone formation and the need for surgery.

Does Tiopronin require protection from oxygen during storage?

Yes, the thiol group is susceptible to oxidation, forming disulfide dimers. Store in airtight containers at 2-8°C.

What is the recommended storage temperature for Tiopronin?

Store at 2-8°C (refrigerated). At room temperature, rapid oxidation and degradation occur, leading to loss of reducing activity.

Is Tiopronin stable in solution for oral or injectable use?

Aqueous solutions oxidize rapidly. Use immediately after preparation. Adding antioxidants (e.g., EDTA) improves short-term stability.

How is the impurity tiopronin dimer (an oxidation product) monitored?

This primary degradation product is specifically quantified using a stability-indicating HPLC method with electrochemical detection, ensuring it remains below pharmacopoeial limits.